A number of years ago, I was at a Purim party and a male friend attended wearing a dress, make up, and jewelry. Knowing how thoughtful he always was with regard to everything he did, I commented on how spectacular he looked, and what a great combination the look was on him… I knew that there was a story to hear. Why a story? Surely it was just Purim – the one day of the Jewish year that cross-dressing is permitted; perhaps even encouraged? All in good fun, right?
He looked me in the eye and said, ‘this holiday is a very important day in the year for me. It is the one day of the year when it is officially ok to wear clothes that make me feel most like me. Who I really am. Without it being a big deal. Without being ridiculed, or worrying about whether I’d be fired for wearing these clothes.’
I understood what he was saying. For some people, part of the fun of Purim is dressing up, and sometimes in the clothes most commonly associated with the opposite gender. And, in that context, we usually call that ‘cross dressing’, although ‘drag’ is probably the more accurate terminology for someone who is intentionally wearing the clothing associated with the opposite gender, but doing so in an over-the-top, performative kind of way. But that’s not how my friend was dressed. His clothing was not a covering over of identity for the entertainment of others, but a deeper and truer expression of inner identity – cross dressing as an expression of self.
Through my own experience, I’ve come to believe that some of our deepest spiritual insights come from within – from getting in touch with our deepest sense of self. Perhaps this is the only thing that we can legitimately label ‘true’ in this life. So what do we do when we find something within Jewish tradition that appears to be a God-given statement that is counter to our inner truth?
In Deuteronomy 22:5 it states: ‘A man’s attire shall not be on a woman, nor may a man wear a woman’s garment’. The rabbis of past generations made an exception for Purim as a festival when reality is intentionally turned on its head. Rashi, (c. 1040-1105 C.E.), explains the verse to apply to a specific context: “